Sodium Azide → (2S,4S)-1-tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate

HRID 1269005Notes

Reaction equation

HRID 1269005 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C@@H:4]1[CH2:8][C@@H:7](S(C)(=O)=O)[CH2:6][N:5]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:20])[C@@H:4]1[CH2:8][C@H:7]([N:21]=[N+:22]=[N-:23])[CH2:6][N:5]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 667719431-tert-Butyl 2-methyl (2S,4R)-4-methanesulfonylpyrrolidine-1,2-dicarboxylate

Product 1

HCID 11219435(2S,4S)-1-tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Boc-(2S,4R)-4-methanesulfonylproline methylester was taken in DMF (10 mL) to which sodium azide (1.30 g, 20.0 mmol) was added and heated at 75–80° C. overnight. DMF was removed and the product was extracted with ethyl acetate (100 mL) and washed with water (50 mL). The azide product 9c (P=Boc, m=1, R9=azide) was obtained (0.98 g, 90%) on removal of solvent.

Workup

  1. additionwas added
  2. temperatureheated at 75–80° C. overnight
  3. customDMF was removed
  4. extractionthe product was extracted with ethyl acetate (100 mL)
  5. washwashed with water (50 mL)

Sources & evidence

ORD record
ord-229874ac49bf4068bbb088603c93c5bd
Source dataset
uspto-grants-2007_04
Patent number
US07199106B2

Reaction notes

Loading…